I began a futile search for a Markdown editor that could automatically generate section numbers and a table of contents. Next I tried "software for technical writing" which turned up some promisingtools. But it wasn’t until I tried searching for

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1.1. Python

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Exactly what I was after - crazy-simple syntax with automatic section numbering and TOC generation (bonus: it also inserts "Last updated datetime" at the bottom).

Quotes & Articles

"Use 'asciidoc' for document markup. Really. It’s actually readable by humans, and easier to parse and way more flexible than XML." -- Linus Torvalds in a reply to his Google+ post

"If Markdown is a 1st-grader, then AsciiDoc is [a] PhD student." -- Dan Allen in a Google+ post

Living the Future of Technical Writing "The issue with Markdown was that it was too simple. It didn’t specify things like table formatting, cross references, indexing, callouts, source code examples, etc. All of which Asciidoc does in a format that is just as easy to write."

And for everything else, there's AsciiDoc.0 "For an extra five minutes learning you get a boatload (think container ship) more features1 - it compiles to DocBook: a mature, actually standardised, highly structured format, and from that you get HTML, EPUB, PDF, slideshows, and man pages for free.0 For math you get MathML, ASCIIMath, and LaTeX (along with a number of ways to render them.) It has a super nice syntax, is equally good at little docs and huge books, and you could theoretically write a proper academic paper in it with the LaTeX backend. And you always know what's going to happen when you try to mix bold and italic... Also endorsed by Linus.2

On PDF output: "If you want to publish HTML, it’s great. For PDF the current way to go it is to compile to DocBook and from DocBook to PDF."

According to the documentation, "Asciidoctor still supports the attribute name 'numbered' to number sections for backward compatibility with AsciiDoc Python, but the name 'sectnums' is preferred." However, I could only get section numbers to appear by using :numbered:, not :sectnums:.